1. Field of the Invention
This invention is directed to new organic compounds and is particularly concerned with novel 1-substituted-6-phenyl-4H-s-triazolo4,3-a][1,4]benzodiazepines and a process for the production thereof.
The novel compounds and the process of production therefor can be illustratively represented as follows: ##STR4## wherein R is selected from the group consisting of hydroxy and alkoxy in which alkyl is of 1 to 3 carbon atoms, inclusive; ##STR5## in which n is zero to 16, ##STR6## in which n' is 2 or 3, and R' is hydrogen or alkyl defined as above benzoyloxy acid, and phenylacetoxy acid; wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive.
The more desirable products of this invention have the formula IV ##STR7## wherein R is selected from the group consisting of hydroxy and alkoxy of 1 to 3 carbon atoms, R.sub.6 and R.sub.7 are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, and NO.sub.2 and wherein R.sub.8 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, NO.sub.2, trifluoromethyl, and alkylthio in which alkyl is of 1 to 3 carbon atoms, inclusive.
Still more desirable are compounds of formula V below: ##STR8## wherein R is selected from the group consisting of hydroxy and alkoxy of 1 to 3 carbon atoms, inclusive; and wherein R.sub.9 and R.sub.10 are selected from the group consisting of hydrogen and chlorine.
The invention includes also the esters of the compounds of formulae III, IV, and V wherein R is hydroxy.
Such esters are those of hydrocarbon carboxylic acids with 1 or 2 carboxyl groups.
For example alkanoic acids of 2 to 18 carbon atoms, inclusive such as acetic, propionic, butyric, valeric, hexanoic, enanthic, caprylic, pelargonic, capric, undecanoic, lauric, tridecanoic, myristic, pentadecanoic, palmitic, margaric, stearic acid; dibasic acids of 4 to 5 carbon atoms, inclusive, such as succinic, and glutaric acids and the aromatic acids of 7 to 8 carbon atoms e.g. benzoic and phenylacetic acids.
The invention further includes the pharmacologically acceptable acid addition salts and N-oxides of compounds of formula III, IV, or V and esters thereof.
The process of this invention comprises: condensing a 1,3-dihydro-5-phenyl-2H-1,4-benzoidazepine-2-thione of formula I in an organic solvent, e.g., a lower-alkanol of 1 to 4 carbon atoms, inclusive, or cyclohexanol with an acid hydrazide II, at a temperature between 60.degree. and 120.degree. C. to give the corresponding 1-substituted 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (III, IV, or V).
Esters of the alcohols and acid addition salts or N-oxides of these compounds are prepared by known conventional means.